注册 English

Colorimetric detection of D-amino acids based on anti-aggregation of gold nanoparticles

Long-Fei Yuan ,  Yu-Jian He ,  Hong Zhao ,  Ying Zhou ,  Pei Gu

downloadPDF
Citation:  Long-Fei Yuan, Yu-Jian He, Hong Zhao, Ying Zhou, Pei Gu. Colorimetric detection of D-amino acids based on anti-aggregation of gold nanoparticles[J]. Chinese Chemical Letters, 2014, 25(7): 995-1000. doi: 10.1016/j.cclet.2014.06.002 shu

Colorimetric detection of D-amino acids based on anti-aggregation of gold nanoparticles

    • 通讯作者: Yu-Jian He,
    Pei Gu,
  • 基金项目:

    This work was supported by the National Natural Science Foundation of China (No. 21272263) (No. 21272263)

    Biomimetic Drugs (No. K20130206) (No. K20130206)

    the University of Chinese Academy of Sciences (No. 08JT011J01)  (No. 08JT011J01)

    the Twelfth Five-Year Plan for National Sciences &Technology Support Project (No. 2012BAI37B03) (No. 2012BAI37B03)

摘要: A new method has been proposed to realize the visual detection of D-amino acids (DAAs) via the antiaggregation of 4-mercaptobenzoic acid modified gold nanoparticles (AuNPs) in the presence of D-amino acid oxidase (DAAO). The negatively charged AuNPs were prepared using sodium citrate as a reducer and stabilizer. The presence of 4-mercaptobenzoic acid (4-MBA) and Cu2+ induces the aggregation of AuNPs, resulting in a color change from ruby red to royal purple. However, DAAO could oxidize DAAs to generate H2O2. In the presence of H2O2, the mercapto (-SH) group in 4-mercaptobenzoic acid can be oxidized to form a disulfide (-S-S-) bond. Based on these facts, the pre-incubation of DAAs and 4-mercaptobenzoic acid with DAAO would significantly reduce the concentration of free 4-mercaptobenzoic acidmolecules, thus the aggregation of AuNPs was interrupted since due to the lack of inducer. As the concentration of DAAs increases, the color of the AuNPs solution would progress from royal purple to ruby red. Consequently, DAAs could be monitored by the colorimetric response of AuNPs using a UV-vis spectrophotometer or even naked eyes. This DAAO mediated visual detectionmethod could determine Dalanine (D-Ala) as a representative DAA with concentrations ranging from 1.5×10-7 mol L-1 to 3.0×10-5 mol L-1, and the detection limit was as low as 7.5×10-8 mol L-1. The proposed method is convenient, low-cost and free of complex equipment, making it feasible to analyze the concentration of D-Ala in real samples of β-amyloid peptide (Aβ1-42).

English

  • 

    1. [1] M. Friedman, Chemistry, nutrition, and microbiology of D-amine acids, J. Agric. Food Chem. 47 (1999) 3457-3479.[1] M. Friedman, Chemistry, nutrition, and microbiology of D-amine acids, J. Agric. Food Chem. 47 (1999) 3457-3479.

    2. [2] C. Henneberger, T. Papouin, S.H.R. Oliet, et al., Long-term potentiation depends on release of D-serine from astrocytes, Nature 463 (2010) 232-236.[2] C. Henneberger, T. Papouin, S.H.R. Oliet, et al., Long-term potentiation depends on release of D-serine from astrocytes, Nature 463 (2010) 232-236.

    3. [3] I. Azua, I. Goiriena, Z. Bana, et al., Release and consumption of D-amino acids during growth of marine prokaryotes, Microb. Ecol. 67 (2014) 1-12.[3] I. Azua, I. Goiriena, Z. Bana, et al., Release and consumption of D-amino acids during growth of marine prokaryotes, Microb. Ecol. 67 (2014) 1-12.

    4. [4] V. Vranova, H. Zahradnickova, D. Janous, et al., The significance of D-amino acids in soil, fate and utilization by microbes and plants: review and identification of knowledge gaps, Plant Soil 354 (2012) 21-39.[4] V. Vranova, H. Zahradnickova, D. Janous, et al., The significance of D-amino acids in soil, fate and utilization by microbes and plants: review and identification of knowledge gaps, Plant Soil 354 (2012) 21-39.

    5. [5] S.A. Fuchs, R. Berger, L.W.J. Klomp, et al., D-amino acids in the central nervous system in health and disease, Mol. Genet. Metab. 85 (2005) 168-180.[5] S.A. Fuchs, R. Berger, L.W.J. Klomp, et al., D-amino acids in the central nervous system in health and disease, Mol. Genet. Metab. 85 (2005) 168-180.

    6. [6] H. Wolosker, E. Dumin, L. Balan, V.N. Foltyn, D-amino acids in the brain: D-serine in neurotransmission and neurodegeneration, FEBS J. 275 (2008) 3514-3526.[6] H. Wolosker, E. Dumin, L. Balan, V.N. Foltyn, D-amino acids in the brain: D-serine in neurotransmission and neurodegeneration, FEBS J. 275 (2008) 3514-3526.

    7. [7] G.H. Fisher, L. Petrucelli, C. Gardner, et al., Free D-amino acids in human cerebrospinalfluid of Alzheimer-disease, multiple-sclerosis, and healthy control subjects, Mol. Chem. Neuropathol. 23 (1994) 115-124.[7] G.H. Fisher, L. Petrucelli, C. Gardner, et al., Free D-amino acids in human cerebrospinalfluid of Alzheimer-disease, multiple-sclerosis, and healthy control subjects, Mol. Chem. Neuropathol. 23 (1994) 115-124.

    8. [8] S. Kato, Y. Kito, H. Hemmi, T. Yoshimura, Simultaneous determination of D-amino acids by the coupling method of D-amino acid oxidase with high-performance liquid chromatography, J. Chromatogr. B 879 (2011) 3190-3195.[8] S. Kato, Y. Kito, H. Hemmi, T. Yoshimura, Simultaneous determination of D-amino acids by the coupling method of D-amino acid oxidase with high-performance liquid chromatography, J. Chromatogr. B 879 (2011) 3190-3195.

    9. [9] C. Mueller, J.R. Fonseca, T.M. Rock, S. Krauss-Etschmann, P. Schmitt-Kopplin, Enantioseparation and selective detection of D-amino acids by ultra-high-performance liquid chromatography/mass spectrometry in analysis of complex biological samples, J. Chromatogr. A 1324 (2014) 109-114.[9] C. Mueller, J.R. Fonseca, T.M. Rock, S. Krauss-Etschmann, P. Schmitt-Kopplin, Enantioseparation and selective detection of D-amino acids by ultra-high-performance liquid chromatography/mass spectrometry in analysis of complex biological samples, J. Chromatogr. A 1324 (2014) 109-114.

    10. [10] Y. Gogami, K. Okada, T. Oikawa, High-performance liquid chromatography analysis of naturally occurring D-amino acids in sake, J. Chromatogr. B 879 (2011) 3259-3267.[10] Y. Gogami, K. Okada, T. Oikawa, High-performance liquid chromatography analysis of naturally occurring D-amino acids in sake, J. Chromatogr. B 879 (2011) 3259-3267.

    11. [11] H. Brückner, A. Schieber, Determination of free D-amino acids in mammalia by chiral gas chromatography-mass spectrometry, J. High Resolut. Chromatogr. 23 (2000) 576-582.[11] H. Brückner, A. Schieber, Determination of free D-amino acids in mammalia by chiral gas chromatography-mass spectrometry, J. High Resolut. Chromatogr. 23 (2000) 576-582.

    12. [12] R. Patzold, H. Bruckner, Gas chromatographic determination and mechanism of formation of D-amino acids occurring in fermented and roasted cocoa beans, cocoa powder, chocolate and cocoa shell, Amino Acids 31 (2006) 63-72.[12] R. Patzold, H. Bruckner, Gas chromatographic determination and mechanism of formation of D-amino acids occurring in fermented and roasted cocoa beans, cocoa powder, chocolate and cocoa shell, Amino Acids 31 (2006) 63-72.

    13. [13] R. Patzold, A. Schieber, H. Bruckner, Gas-chromatographic quantification of free Damino acids in higher vertebrates, Biomed. Chromatogr. 19 (2005) 466-473.[13] R. Patzold, A. Schieber, H. Bruckner, Gas-chromatographic quantification of free Damino acids in higher vertebrates, Biomed. Chromatogr. 19 (2005) 466-473.

    14. [14] C.H. Nieh, Y. Kitazumi, O. Shirai, K. Kano, Sensitive D-amino acid biosensor based on oxidase/peroxidase system mediated by pentacyanoferrate-bound polymer, Biosens. Bioelectron. 47 (2013) 350-355.[14] C.H. Nieh, Y. Kitazumi, O. Shirai, K. Kano, Sensitive D-amino acid biosensor based on oxidase/peroxidase system mediated by pentacyanoferrate-bound polymer, Biosens. Bioelectron. 47 (2013) 350-355.

    15. [15] S. Lata, B. Batra, C.S. Pundir, Construction of D-amino acid biosensor based on Damino acid oxidase immobilized onto poly (indole-5-carboxylic acid)/zinc sulfide nanoparticles hybrid film, Process Biochem. 47 (2012) 2131-2138.[15] S. Lata, B. Batra, C.S. Pundir, Construction of D-amino acid biosensor based on Damino acid oxidase immobilized onto poly (indole-5-carboxylic acid)/zinc sulfide nanoparticles hybrid film, Process Biochem. 47 (2012) 2131-2138.

    16. [16] S. Lata, B. Batra, P. Kumar, et al., Construction of an amperometric D-amino acid biosensor based on D-amino acid oxidase/carboxylated mutliwalled carbon nanotube/ copper nanoparticles/polyalinine modified gold electrode, Anal. Biochem. 437 (2013) 1-9.[16] S. Lata, B. Batra, P. Kumar, et al., Construction of an amperometric D-amino acid biosensor based on D-amino acid oxidase/carboxylated mutliwalled carbon nanotube/ copper nanoparticles/polyalinine modified gold electrode, Anal. Biochem. 437 (2013) 1-9.

    17. [17] E. Rosini, G. Molla, C. Rossetti, et al., A biosensor for all D-amino acids using evolved D-amino acid oxidase, J. Biotechnol. 135 (2008) 377-384.[17] E. Rosini, G. Molla, C. Rossetti, et al., A biosensor for all D-amino acids using evolved D-amino acid oxidase, J. Biotechnol. 135 (2008) 377-384.

    18. [18] Y.C. Cao, R.C. Jin, S. Thaxton, et al., A two-color-change, nanoparticle-based method for DNA detection, Talanta 67 (2005) 449-455.[18] Y.C. Cao, R.C. Jin, S. Thaxton, et al., A two-color-change, nanoparticle-based method for DNA detection, Talanta 67 (2005) 449-455.

    19. [19] H. Chi, B.H. Liu, G.J. Guan, et al., A simple, reliable and sensitive colorimetric visualization of melamine in milk by unmodified gold nanoparticles, Analyst 135 (2010) 1070-1075.[19] H. Chi, B.H. Liu, G.J. Guan, et al., A simple, reliable and sensitive colorimetric visualization of melamine in milk by unmodified gold nanoparticles, Analyst 135 (2010) 1070-1075.

    20. [20] F. Li, Y. Feng, C. Zhao, et al., Simple colorimetric sensing of trace bleomycin using unmodified gold nanoparticles, Biosens. Bioelectron. 26 (2011) 4628-4631.[20] F. Li, Y. Feng, C. Zhao, et al., Simple colorimetric sensing of trace bleomycin using unmodified gold nanoparticles, Biosens. Bioelectron. 26 (2011) 4628-4631.

    21. [21] C.D. Medley, J.E. Smith, Z. Tang, et al., Gold nanoparticle-based colorimetric assay for the direct detection of cancerous cells, Anal. Chem. 80 (2008) 1067-1072.[21] C.D. Medley, J.E. Smith, Z. Tang, et al., Gold nanoparticle-based colorimetric assay for the direct detection of cancerous cells, Anal. Chem. 80 (2008) 1067-1072.

    22. [22] H. Li, Y.W. Yang, Gold nanoparticles functionalized with supramolecular macrocycles, Chin. Chem. Lett. 24 (2013) 545-552.[22] H. Li, Y.W. Yang, Gold nanoparticles functionalized with supramolecular macrocycles, Chin. Chem. Lett. 24 (2013) 545-552.

    23. [23] B.H. Wu, H.Y. Yang, H.Q. Huang, et al., Solvent effect on the synthesis of monodisperse amine-capped Au nanoparticles, Chin. Chem. Lett. 24 (2013) 457-462.[23] B.H. Wu, H.Y. Yang, H.Q. Huang, et al., Solvent effect on the synthesis of monodisperse amine-capped Au nanoparticles, Chin. Chem. Lett. 24 (2013) 457-462.

    24. [24] S. Link, M.A. El-Sayed, Spectral properties and relaxation dynamics of surface plasmon electronic oscillations in gold and silver nanodots and nanorods, J. Phys. Chem. B 103 (1999) 8410-8426.[24] S. Link, M.A. El-Sayed, Spectral properties and relaxation dynamics of surface plasmon electronic oscillations in gold and silver nanodots and nanorods, J. Phys. Chem. B 103 (1999) 8410-8426.

    25. [25] Y.P. Li, L. Jiang, T. Zhang, et al., Colorimetric detection of glucose using a boronic acid derivative receptor attached to unmodified AuNPs, Chin. Chem. Lett. 25 (2014) 77-79.[25] Y.P. Li, L. Jiang, T. Zhang, et al., Colorimetric detection of glucose using a boronic acid derivative receptor attached to unmodified AuNPs, Chin. Chem. Lett. 25 (2014) 77-79.

    26. [26] R. Elghanian, J.J. Storhoff, R.C. Mucic, et al., Selective colorimetric detection of polynucleotides based on the distance-dependent optical properties of gold nanoparticles, Science 277 (1997) 1078-1081.[26] R. Elghanian, J.J. Storhoff, R.C. Mucic, et al., Selective colorimetric detection of polynucleotides based on the distance-dependent optical properties of gold nanoparticles, Science 277 (1997) 1078-1081.

    27. [27] C.Y. Lin, C.J. Yu, Y.H. Lin, W.L. Tseng, Colorimetric sensing of silver(I) and mercury(II) ions based on an assembly of Tween 20-stabilized gold nanoparticles, Anal. Chem. 82 (2010) 6830-6837.[27] C.Y. Lin, C.J. Yu, Y.H. Lin, W.L. Tseng, Colorimetric sensing of silver(I) and mercury(II) ions based on an assembly of Tween 20-stabilized gold nanoparticles, Anal. Chem. 82 (2010) 6830-6837.

    28. [28] N. Ding, H. Zhao, W.B. Peng, et al., A simple colorimetric sensor based on antiaggregation of gold nanoparticles for Hg2+ detection, Colloids Surf. A-Physicochem. Eng. Aspect 395 (2012) 161-167.[28] N. Ding, H. Zhao, W.B. Peng, et al., A simple colorimetric sensor based on antiaggregation of gold nanoparticles for Hg2+ detection, Colloids Surf. A-Physicochem. Eng. Aspect 395 (2012) 161-167.

    29. [29] J.S. Lee, M.S. Han, C.A. Mirkin, Colorimetric detection of mercuric ion (Hg2+) in aqueous media using DNA-functionalized gold nanoparticles, Angew. Chem. Int. Ed. 46 (2007) 4093-4096.[29] J.S. Lee, M.S. Han, C.A. Mirkin, Colorimetric detection of mercuric ion (Hg2+) in aqueous media using DNA-functionalized gold nanoparticles, Angew. Chem. Int. Ed. 46 (2007) 4093-4096.

    30. [30] Y. Xue, H. Zhao, Z.J. Wu, et al., Colorimetric detection of Cd2+ using gold nanoparticles cofunctionalized with 6-mercaptonicotinic acid and L-cysteine, Analyst 136 (2011) 3725-3730.[30] Y. Xue, H. Zhao, Z.J. Wu, et al., Colorimetric detection of Cd2+ using gold nanoparticles cofunctionalized with 6-mercaptonicotinic acid and L-cysteine, Analyst 136 (2011) 3725-3730.

    31. [31] Y. Zhou, P.L. Wang, X.O. Su, et al., Colorimetric detection of ractopamine and salbutamol using gold nanoparticles functionalized with melamine as a probe, Talanta 112 (2013) 20-25.[31] Y. Zhou, P.L. Wang, X.O. Su, et al., Colorimetric detection of ractopamine and salbutamol using gold nanoparticles functionalized with melamine as a probe, Talanta 112 (2013) 20-25.

    32. [32] X.F. Zhang, H. Zhao, Y. Xue, et al., Colorimetric sensing of clenbuterol using gold nanoparticles in the presence of melamine, Biosens. Bioelectron. 34 (2012) 112-117.[32] X.F. Zhang, H. Zhao, Y. Xue, et al., Colorimetric sensing of clenbuterol using gold nanoparticles in the presence of melamine, Biosens. Bioelectron. 34 (2012) 112-117.

    33. [33] X.F. Zhang, Y. Zhang, H. Zhao, et al., Highly sensitive and selective colorimetric sensing of antibiotics in milk, Anal. Chim. Acta 778 (2013) 63-69.[33] X.F. Zhang, Y. Zhang, H. Zhao, et al., Highly sensitive and selective colorimetric sensing of antibiotics in milk, Anal. Chim. Acta 778 (2013) 63-69.

    34. [34] X.F. Zhang, Z.J. Wu, Y. Xue, et al., Colorimetric detection of melamine based on the interruption of the synthesis of gold nanoparticles, Anal. Methods 5 (2013) 1930-1934.[34] X.F. Zhang, Z.J. Wu, Y. Xue, et al., Colorimetric detection of melamine based on the interruption of the synthesis of gold nanoparticles, Anal. Methods 5 (2013) 1930-1934.

    35. [35] Z.J. Wu, H. Zhao, Y. Xue, et al., Colorimetric detection of melamine during the formation of gold nanoparticles, Biosens. Bioelectron. 26 (2011) 2574-2578.[35] Z.J. Wu, H. Zhao, Y. Xue, et al., Colorimetric detection of melamine during the formation of gold nanoparticles, Biosens. Bioelectron. 26 (2011) 2574-2578.

    36. [36] Q.A. Cao, H. Zhao, Y.J. He, et al., Hydrogen-bonding-induced colorimetric detection of melamine by nonaggregation-based Au-NPs as a probe, Biosens. Bioelectron. 25 (2010) 2680-2685.[36] Q.A. Cao, H. Zhao, Y.J. He, et al., Hydrogen-bonding-induced colorimetric detection of melamine by nonaggregation-based Au-NPs as a probe, Biosens. Bioelectron. 25 (2010) 2680-2685.

    37. [37] Y. Zhou, H. Zhao, Y.J. He, N. Ding, Q. Cao, Colorimetric detection of Cu2+ using 4-mercaptobenzoic acid modified silver nanoparticles, Colloid Surf. A-Physicochem. Eng. Aspect 391 (2011) 179-183.[37] Y. Zhou, H. Zhao, Y.J. He, N. Ding, Q. Cao, Colorimetric detection of Cu2+ using 4-mercaptobenzoic acid modified silver nanoparticles, Colloid Surf. A-Physicochem. Eng. Aspect 391 (2011) 179-183.

    38. [38] Y.C. Shiang, C.C. Huang, H.T. Chang, Gold nanodot-based luminescent sensor for the detection of hydrogen peroxide and glucose, Chem. Commun. (2009) 3437-3439.[38] Y.C. Shiang, C.C. Huang, H.T. Chang, Gold nanodot-based luminescent sensor for the detection of hydrogen peroxide and glucose, Chem. Commun. (2009) 3437-3439.

    39. [39] A.R. Quesada, R.W. Byrnes, S.O. Krezoski, et al., Direct reaction of H2O2 with sulfhydryl groups in HL-60 cells: zinc-metallothionein and other sites, Arch. Biochem. Biophys. 334 (1996) 241-250.[39] A.R. Quesada, R.W. Byrnes, S.O. Krezoski, et al., Direct reaction of H2O2 with sulfhydryl groups in HL-60 cells: zinc-metallothionein and other sites, Arch. Biochem. Biophys. 334 (1996) 241-250.

    40. [40] B. Cardey,M. Enescu, Selenocysteine versus cysteine reactivity: a theoretical study of their oxidation by hydrogen peroxide, J. Phys. Chem. A 111 (2007) 673-678.[40] B. Cardey,M. Enescu, Selenocysteine versus cysteine reactivity: a theoretical study of their oxidation by hydrogen peroxide, J. Phys. Chem. A 111 (2007) 673-678.

    41. [41] J. Wang, D.M. Wang, Y.F. Li, Study of cysteine modified gold nanoparticles as a colorimetric detection platform for oxidants, Chin. Sci. Bull. 56 (2011) 1196-1203.[41] J. Wang, D.M. Wang, Y.F. Li, Study of cysteine modified gold nanoparticles as a colorimetric detection platform for oxidants, Chin. Sci. Bull. 56 (2011) 1196-1203.

    42. [42] L.F. Yuan, Y.J. He, Effect of surface charge of PDDA-protected gold nanoparticles on the specificity and efficiency of DNA polymerase chain reaction, Analyst 138 (2013) 539-545.[42] L.F. Yuan, Y.J. He, Effect of surface charge of PDDA-protected gold nanoparticles on the specificity and efficiency of DNA polymerase chain reaction, Analyst 138 (2013) 539-545.

    43. [43] X.H. Ji, X.N. Song, J. Li, et al., Size control of gold nanocrystals in citrate reduction: the third role of citrate, J. Am. Chem. Soc. 129 (2007) 13939-13948.[43] X.H. Ji, X.N. Song, J. Li, et al., Size control of gold nanocrystals in citrate reduction: the third role of citrate, J. Am. Chem. Soc. 129 (2007) 13939-13948.

    44. [44] A. Daniello, A. Vetere, G.H. Fisher, et al., Presence of D-alanine in proteins of normal and Alzheimer human brain, Brain Res. 592 (1992) 44-48.[44] A. Daniello, A. Vetere, G.H. Fisher, et al., Presence of D-alanine in proteins of normal and Alzheimer human brain, Brain Res. 592 (1992) 44-48.

    45. [45] K. Wiesehan, K. Buder, R.P. Linke, et al., Selection of D-amino-acid peptides that bind to Alzheimer's disease amyloid peptide Aβ1-42 by mirror image phage display, Chembiochem 4 (2003) 748-753.[45] K. Wiesehan, K. Buder, R.P. Linke, et al., Selection of D-amino-acid peptides that bind to Alzheimer's disease amyloid peptide Aβ1-42 by mirror image phage display, Chembiochem 4 (2003) 748-753.

    46. [46] Y.S. Shim, W.J. Yoon, J. Ha, et al., Method validation of 16 types of structural amino acids using an automated amino acid analyzer, Food Sci. Biotechnol. 22 (2013) 1567-1571.[46] Y.S. Shim, W.J. Yoon, J. Ha, et al., Method validation of 16 types of structural amino acids using an automated amino acid analyzer, Food Sci. Biotechnol. 22 (2013) 1567-1571.

    47. [47] S.V. Khoronenkova, V.I. Tishkov, D-amino acid oxidase: physiological role and applications, Biochemistry (Mosc.) 73 (2008) 1511-1518.[47] S.V. Khoronenkova, V.I. Tishkov, D-amino acid oxidase: physiological role and applications, Biochemistry (Mosc.) 73 (2008) 1511-1518.

  • 加载中
WeChat 扫一扫看文章
计量
  • PDF下载量:  0
  • 文章访问数:  1440
  • HTML全文浏览量:  26
文章相关
  • 收稿日期:  2014-04-01
  • 网络出版日期:  2014-05-28
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章

All Rights Reserved by the Chinese Chemical Society   中国化学会 版权所有 京ICP备05002797号

本系统由北京仁和汇智信息技术有限公司开发    技术支持: info@rhhz.net